Thionyl Chloride → 5-(Aminosulphonyl)-2-methoxybenzoyl chloride

HRID 1282907Notes

Reaction equation

HRID 1282907 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:8][C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:18])=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:8][C:4]=1[C:5]([Cl:18])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 896012-Methoxy-5-sulfamoylbenzoic acid

Product 1

HCID 1042285-(Aminosulphonyl)-2-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the so-obtained 2-methoxy-5-sulfamoyl benzoic acid in 600 parts of anhydrous tetrahydrofuran, there were added rapidly 27.5 parts of thionyl chloride. The mixture was refluxed for 2 hours. The solution was then evaporated under vacuo. The residue was treated with 500 parts of anhydrous benzene. After elimination of benzene in vacuo, there were obtained 29 parts of 2-methoxy-5-sulfamoyl benzoyl chloride, M.P. 148°-150° C, which after one recrystallization from benzene melts at 156° C.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. customThe solution was then evaporated under vacuo
  3. additionThe residue was treated with 500 parts of anhydrous benzene

Sources & evidence

ORD record
ord-234988613c764d64a17b0431ff1e2345
Source dataset
uspto-grants-1976_08
Patent number
US03972994

Reaction notes

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